It's true it's easier to build your system in small pieces as you discover your needs, but it helps a ton to have a better idea of what can be accomplished through customization.

In my case, I didn't write any Elisp between 2004-2010 and probably used Org mode as a bullet list during that time. Until I had enough interest to read its documentation and explored how others are using it.

Only then was I able to come up with a half-decent solution that was still quite good, but really so far off of what can be accomplished with a better understanding of the parts at play in this mode, as demonstrated by Bernt Hanson's setup (http://doc.norang.ca/org-mode.html).

To this day I'm not even considering trying to rethink the way he is using Org mode because his setup works out perfectly for me, and I have to GTD like everybody else.

All I'm saying is it may not be obvious at first glance and without studying documentation but a very powerful set of tools are available in there and anyone with half a brain can use them, and that it's best to adopt complex-type configurations once you've wrapped your head around them.